Abstract
The reaction of electron-rich arenes with alkali metal bromides such as sodium and potassium bromides in the presence of conc. H2SO4 to give p-bromoarenes is reported. The reaction is possible in the absence of any specialised oxidising agents and the yields are high.
References
1.
Srebnik M.
,
Mechoulam R.
, and
Yana I.
, J. Chem. Soc., Perkin Trans. 1. , 1987 , 1423 .
2.
Norman R.O. C.
, and
Taylor R.
, Electrophilic Substitution in Benzenoid Compounds , Elsevier , New York , 1965 , 130 .
3.
March J.
, Advanced Organic Chemistry , John Wiley & Sons, Inc. , New York , 4th edn, 1992 , 531 .
4.
Siddiq M.
,
Khan S. A.
, and
Munawar M. A.
, J. Org. Chem. , 1988 , 53 , 1799 .
5.
Prestwich G.D.
,
Dorman G.
,
Olszewski J. D.
,
Hong Y.
, and
Ahern D. G.
, J. Org. Chem. , 1995 , 60 , 2292 .
6.
Mattern D.L.
, J. Org. Chem. , 1983 , 48 , 4772 .
7.
Minisci F.
,
Vismara E.
, and
Fontana F.
, J. Chem. Soc., Perkin Trans. 2 , 1989 , 1246 .
8.
McKillop A.
,
Bromley D.
, and
Taylor E. C.
, J. Org. Chem. , 1972 , 37 , 88 .
9.
Mitchell R.H.
,
Lai Y. H.
, and
Williams R. V.
, J. Org. Chem. , 1979 , 44 , 4733 .
10.
Ranu C.B.
,
Sarkar C. D.
, and
Chakraborthy R.
, Syn. Commun. , 1992 , 22 , 1095 .
11.
Fieser L.F.
, and
Fieser M.
, Reagents for Organic Synthesis , John Wiley and Sons , New York , 1967 , 885 , 1144 .
12.
Kajigaeshi S.
,
Moriwaki M.
,
Tanaka T.
, and
Fujisaki S.
, J. Chem. Soc., Perkin Trans. 1 , 1990 , 897 .
13.
Berthelot J.
,
Guette C.
,
Desbene P. L.
,
Basselier J. J.
,
Chaquin P.
, and
Masure D.
, Can. J. Chem. , 1989 , 67 , 2061 .
14.
Kajigaeshi S.
,
Kakinami T.
,
Yamasaki H.
,
Fujisaki S.
, and
Okamoto T.
, Bull. Chem. Soc. Jpn , 1988 , 61 , 2681 .
15.
Gervat S.
,
Leonel E.
,
Barraud J. Y.
, and
Ratovelomanana V.
, Tetrahedron Lett. , 1993 , 34 , 2115 .
16.
Kajigaeshi S.
,
Kakinami T.
,
Inoue K.
,
Kondo M.
,
Nakamura H.
,
Fujikawa M.
, and
Okamoto T.
, Bull. Chem. Soc. Jpn , 1988 , 61 , 597 .
17.
Kajigaeshi S.
,
Kakinami T.
,
Nakamura H.
,
Fujikawa M.
, and
Okamoto T.
, Bull. Chem. Soc. Jpn , 1987 , 60 , 4187 .
18.
Furia F.D.
,
Conte V.
, and
Moro S.
, Tetrahedron Lett. , 1994 , 35 , 7429 .
19.
Sommer J.
,
Culmann J. C.
, and
Cherry G.
, Tetrahedron Lett. , 1990 , 31 , 2007 .
20.
Holmberg K.
,
Currie F.
, and
Westman G.
, Colloids and Surface A: Physicochem Eng Aspects. , 2003 , 215 , 51 .
21.
Mosnaim D.
, and
Nonhebel D. C.
, Tetrahedron. , 1969 , 25 , 1591 .
22.
Nagaraja D.
, and
Pasha M. A.
, Tetrahedron Lett. , 1999 , 40 , 7855 .
23.
Rama K.
,
Nagendra E.
, and
Pasha M. A.
, Ind. J. Chem. , 2000 , 39B , 563 .
24.
Nagaraja D.
, and
Pasha M. A.
, Ind. J. Chem. , 2002 , 41B , 1747 .
25.
Nagaraja D.
, and
Pasha M. A.
, J. Saudi Chem. Soc. , 2003 , 7 , 99 .
26.
Pasha M.A.
, and
Myint Y. Y.
, Ind. J. Chem. , 2004 , 43B , 357 .
27.
Sykes P.
, A Guidebook to Mechanism in Organic Chemistry , 6th edn, Pearson Education , India , 2004 , 163 .
28.
Soni P.L.
, Text book of Inorganic Chemistry , 5th edn. Delhi , 1970 , 78 .
29.
Vogel I.
, A Text book of Practical Organic Chemistry , 3rd edn, Longman Group Limited , London , 1975 , 86 .
30.
Dorpat J.N.
, Ber. , 1919 , 52B , 1028 .
31.
Kovacic P.
, and
Davis K. E.
, J. Am. Chem. Soc. , 1964 , 86 , 427 .
32.
Klarmann P.
, J. Am. Chem. Soc. , 1933 , 55 , 4657 .
33.
Varma P.S.
,
Mozumdar D. N.
, and
Rajah K. K.
, J. Ind. Chem. Soc. , 1933 , 10 , 595 .
34.
Bisarya S.C.
, and
Rao R.
, Syn. Commun. , 1993 , 23 , 779 .
35.
Simons W.W.
, Sadtler Handbook of Infrared Spectra , Sadtler Research Laboratories Inc , Philadelphia, U.S.A , 1978 , 109 .
